Filmmaker Michelle Ortega finds it better to interview her subjects in their natural setting. She sits on the couch of her apartment, where she crafts the concepts and rough cuts of her films – her own natural setting.

For Michelle Ortega, being a single teenager seemed much easier than getting back into the dating world as a middle-aged woman. Cheesy romance movies from the 1970s seemed realistic. Life would be complete if she married any of the members of Duran Duran. Drinking 3 a.m. peppermint shots, passing out, and being carried home by a teenage playboy to her angry mother counted as a first date. Charmingly picking up the “sweet, good-looking” guy who worked at the deli led to her first boyfriend at age 16. And for Ortega, as longtime best friend Christy Dobbs said, older guys embodied the ideal.

“Growing up, Michelle was always beautiful and always being flirted with, pursued and had lots of choices about what boys to date,” said Dobbs.

Today, most of Ortega’s dating history consists of her high school days dating boys in and around her hometown of Felton in Santa Cruz, California and while studying Radio and Television at San Francisco State University where she met her college sweetheart and now-ex-husband.

While working on school video projects at SFSU, project partner Jason Blatt became her boyfriend of five years, fiancé, and then husband. The two founded video production company North Beach Digital in 2009 in San Francisco, where they lived together until the couple’s split in 2012. While still working as an award-winning video producer for Google and co-owning North Beach Digital, Ortega made the decision to move across the country to New York City shortly after.

28 years after her first date and in a new city, Ortega finds herself looking for her second chance at love. The native Californian realized she did not gain as much dating experience as her peers by marrying out of college.

When it comes to dating and being single again, the 44-year-old Ortega said, “I don’t know what I’m doing. I don’t know how to do it. I haven’t done it since I was like a really young person, by my age as standards. And that’s what I wanted to explore. What am I doing? How do I do it? How are people handling it?”

Like Ortega, the love lives of single women involve the ups and downs of relationships. No matter their sexuality, ethnicity, or age, each carries with them experiences that shape their outlook on dating. The filmmaker wanted to know their hardships and why they were still motivated to keeping looking for “the one.” These thoughts inspired her global initiative to expose the truths of dating for single women in a series of feature-length documentaries entitled “The Single Ladies.” And with Ortega’s recent move to the West Village, New York City women would be the first to dish on “The Single Ladies of New York.”

Acting as director and producer, Ortega spent four days in Gramercy, Harlem, Midtown, and Williamsburg interviewing women on their dating perspectives, hoping filming would shed some light on her own love life.

“Whenever I’ve seen when people are single, it’s fun or entertaining. Being on my own, I didn’t like just the idea of flirting and meeting people. I just don’t know. It just didn’t appeal to me,” said Ortega.

From Match.com to casually dating locals, those close to the video producer encouraged her to break her shyness during her first few weeks in the city. Soon after, Ortega met her current boyfriend and the audio operator of her documentary, David Tews, through a friend. Ortega and Tews moved in together in April 2014.

Yet, Ortega said she still does not understand why so many women enjoy modern-day dating rituals. To the video producer, there must be some reason why real-life women ranging from their 20s to 60s get back in the dating world despite mishaps, awkwardness, and heartbreak. And noticing in New York the lack of people willing to settle down, single women in the city intrigued her.

Friends referred her to singles willing to be interviewed. At the nail salon one day, Ortega even consulted her manicurist for an interview. A connection linked her to dating expert, Charreah Jackson, who also offered commentary in the film.

Though the interviewees were of various ages and sexualities, and randomly found, everyone desired somebody of their own to love, according to Ortega.

“I liked how honest everyone was. It’s not easy to put your social life in the spotlight willingly like that. These are all great ladies trying to find a partner to share their lives with. I think the main thing I learned more so than what the ladies revealed, is that dating requires being patient and care not to get frustrated. Everyone dating is looking for something but it takes time,” said Tews.

Advice from 59-year-old Single Lady of New York, Dorit Koppel, stayed with Ortega. Koppel reflected on the evanescence of relationships and how acceptance of this fact is key in dating.

The basis of interviewing would be a setting that each woman felt natural to them and free-form conversations erupting for the questions Ortega sent ahead of time: “Did you ever experience loneliness and what is that like? Do you believe in soulmates? What factor do you think your age plays in dating? What do you think are the benefits and difficulties in dating in New York in particular?”

Specifically, Ortega awaited finding out the difference between dating in your twenties and sixties. But she said she felt that she could not come to a conclusion until more interviews were shot.

Filming so far included women of various ages, ethnicities, body types, and experiences. Ortega hopes to interview those in the lesbian, gay, bisexual, and transgender community as well as men for insights.

For the production of the film, the filmmaker relied on funding from a Kickstarter campaign, a website-based plea for benefactors, or “backers,” to support start-ups and project. Ortega set a goal of 25,000 dollars for backers to donate by deadline March 17. She also had faith in finding an expert in publicity to join the crew.

The funds from the campaigned would be allocated: 5,000 dollars for four more days of shooting; 10,000 towards editing; 2,500 dollars to supply gifts for backers; 2,000 dollars for graphics animation and archival footage usage; 3,000 dollars for music licensing and Error & Omissions insurance; and 2,500 towards marketing and film festivals submissions.

As backers gradually pledged donations, Ortega stopped waiting for her first ever Kickerstarter campaign to gain the desired momentum and started shooting with her own money.

In only four days of self-funded shooting, Ortega lead a crew of five others including: Directors of Photography Svetlana Cvetco, who has worked on Oscar and Sundance Festival winning films, and Norm Magnuson, a former cinematographer and producer for Google; Gaffer Chris Turiello; and Audio Operators Tews and Heather Duthie. A friend of Ortega’s helped with the publicity. Ortega also edited the rough cut of what she had so far.

Within just the beginning stages of filming, “The Single Ladies of New York” already caught media attention. Articles, cable television shows, and internet radio broadcasts reported on the upcoming documentary. New York Woman in Film and Television tweeted about it. Ortega’s excitement grew after a retweet from Sex and the City author, Candace Bushnell.

Excitement grew over Ortega’s proposed plot to accurately represent women finding love in ways that reality shows and movies failed to accomplish. She also wants women from all ages to realize their beauty, that they should seek to find passions outside their relationships as well, and that they can be both alone and happy.

“I would want Michelle to learn about how to take a subject that is overdone and bring her unique voice to it – in a way that is as optimistic, realistic and fun-loving as she is, but doesn’t ignore the pain and suffering that I know is part of being single anywhere – especially as you approach middle age,” said Dobbs.

She originally planned for “The Single Ladies of New York,” under the production company for her independent films Hip Chicks Flicks, to be completed by October 2014 just in time to be shown at the Tribeca Film Festival, the New York Film Festival, LUNAFEST, and Rooftop Films.

But Ortega simultaneously working full-time at Google and advancing North Beach Digital combined with the lack of Kickstarter pledges halted further filming.

“Well the day of [the deadline], I’m like I’m not gonna meet my goal; unless somebody drops outta the sky and hands me a bunch of money, it’s not gonna happen. But I still kept reaching out to people and promoting it because you never know. And at least if I don’t meet my goal today, more people are going to know for next time,” said Ortega.

“The Single Ladies of New York” missed its deadline, having only 64 backers and 8,608 dollars – about one fourth of Ortega’s goal.

“The day after, I was pretty exhausted. I’m just like I just need a little break. There were a lot of people who were reaching out and it was very kind and they were saying, ‘Look, I still wanna donate even though you didn’t reach your goals.’ But at that time, I’m like this is great but, I ‘m gonna set this all aside and respond to people and then give myself a little break before I jump back in,” said Ortega.

With the unsuccessful Kickstarter campaign, Ortega pushed back the film’s debut date until next year and strategized her production plans in advance for future campaigns for the film. She wanted to give herself “more time to just make the next round of funds,” inspired by a friend who organized the logistics of his project a year before having a successful campaign. The filmmaker anticipates premiering “The Single Ladies of New York” between January and February 2014, but has not officially set a date yet. But this time, she plans on building fanbases, reaching out to bloggers, and getting people to write about the film pre-hand, labeling her Kickstarter campaign as a “big lesson in [early] marketing and promotion.”

“I would have had the ducks lined up before I started as far as building communities of people and making connections with people who have access to larger numbers of people and audiences that apply to my subject. Because trying to do that when it’s already starting was crazy because it takes so much work and dedication and time,” said Ortega.

Another mistake the video producer acknowledges is that her goal sum was too high. She plans on maker several smaller campaigns and breaking up production for the film.

“What is the strategy I’m doing to get it out there? The first thing being, I’m gonna start in smaller chunks. I’m just impatient and I just wanna do it,” said Ortega.

As of May, the video producer received donations outside of Kickstarter and help from a marketing and promotion professional. Ortega said she feel she has enough funds for the next set of shoots and set a date for filming again.

“I can’t wait until everything’s like done. I need to work on the film. That’s my primary passion. I think with any artist, filmmaker, otherwise, that’s a huge challenge because that’s not the stuff you wanna focus on, but it’s so key in helping to make your work happen,” said Ortega.

For Ortega, it is never too late for a second chance, no matter what passion you are working towards and how much time it will take.

After finishing “The Single Ladies of New York,” Ortega has plans to film the next part of the series in California.